Success Advice
A Salesman’s Guide to Everyday Conversation With Strangers

One of the most valuable traits a salesperson can possess is the ability to easily strike up conversations with anyone who crosses their path. Whether you’re on a plane or in line at the grocery store, having a method for starting a conversation with random strangers is an asset that sets the best apart from the mediocre. This ability correlates into more sales as every new person you talk to becomes a new prospect for you to pitch your services to.
Since sales is something that all of us do every single day (you do not have to always be bartering or selling something for money to be selling something), the five steps below have proven to help out a lot of people with their sales career and confidence to network when around people they don’t know.
Here are my 5 proven steps to starting a conversation with anyone:
1. Paralleling
This step is super effective and easy. The trick is identifying what the other person cares about. Things like tattoos and jewelry are great examples of personal attributes or items that they cherish and or that mean something to them.
Ideally, you want to identify something they have that you have yourself. This becomes an easy way to strike up a conversation and build rapport by being “like” them. For example, on a recent trip, I noticed that the guy sitting next to me had Chinese characters in the tattoo on his arm. From here, we can move into…
2. 20 Questions
Here we start asking them questions about the item or attribute that we identified in the paralleling step. Be sure to make eye contact, smile and approach the questions with a relaxed, yet interested energy. If they feel like you are forcing the conversation, it will make them uncomfortable and clam up.
Remember the tattooed guy on the plane? After I asked him what the Chinese characters meant, the door was open to ask further questions, like “That’s really cool, what made you get the tattoo?”
To make it easy, create questions fusing who, what, when, where and how, which allows the person you’re talking to to tell a story about themselves. This creates a bond and builds trust with them quickly because they feel admired and liked. You’d also be amazed at how much you can find out about someone by doing this.
However there is a warning here! There is a way to screw this up! The item or attribute you are paralleling needs to be something you genuinely like and are interested in. This is key. So if you know nothing about tattoos, don’t want a tattoo, or don’t like tattoos, then don’t compliment them on their tattoo, because it will be disingenuous and you won’t be contribute back to the conversation. In other words, you will lose the bond with the person you are communicating with really quickly.
“To be interesting, be interested.” – Dale Carnegie
3. You’re My Hero
If you have asked enough questions you should have a general idea from the person you are talking to and you now can use that information to connect with them on other levels of common interest.
Find life circumstances that match or stories that you share. Tell them how something in their story moved you emotionally (make sure to be genuine!) or help the person emotionally see and feel how their story connected with you. This will help to initiate the first “bonding moment” that you two share.
We call this step of this process, “you’re my hero” because you have shown excitement around something they do that you wish to do or do yourself. This “likeness” helps strengthen the bond and open up the other person to share more about their life with you.
4. Common Denominators
By now you’ve asked some questions, gotten some information from them, and heightened the bond between the two of you. You can keep the conversation going by mentioning other things that you like and notice that you two might have in common, based either on physical things you see or answers to your questions.
Each “common denominator” you can find serves to tighten the bond between you and them. The stronger the bond you can develop with them, the more powerful the last step will be!
“You can make more friends in two months by becoming interested in other people than you can in two years by trying to get other people interested in you.” – Dale Carnegie
5. Leave Behind
Here is where you make this conversation stick in their memory. All four others steps lead to this, because it’s where you can leverage the conversation and connection into some sort of transaction.
This transaction doesn’t always mean a sale, it can occur in a range of ways. You may have a person to introduce them to that can solve their challenge, or you may be able to send them a referral, or it could be as simple as a business card exchange or friending them on social media.
A popular leave behind in 2019 is a mobile app, mainly because someone always has their phone with them. A leave behind is a way for them to have your contact information (and you get theirs) so you can connect with them after the conversation is over. Other great leave behinds are a copy of a book you wrote, your website link, or a sales funnel link.
Sometimes too, when things go really well with the conversation (believe me, you will know) you may be able to immediately schedule a time to talk with them later. The bond needs to be strong enough before you propose this because if it’s not it can ruin this entire opportunity.
If you’re thinking this sounds simple, you’re right! And it still takes practice to perfect. For some seasoned sales people, they can probably think back to a time or two when they did this unconsciously and it worked out great. The thing is, when you practice these steps and allow it to become an unconscious process you can use too, it can be a lethal weapon for you in your professional career and your life as a whole.
Start by practicing the steps consistently. Practice at the gym, at restaurants, anywhere you are where there is a stranger nearby. Over a short period of time you’ll accrue a lot more contacts, have the opportunity to make more sales and you’ll become such a natural that people will think you were born charismatic!
What part of this salesman’s guide resonated most with you and why? Share your thoughts with us below!
Success Advice
Why One-Size-Fits-All Leadership Will Always Fail (and What Works Instead)
The surprising truth about leadership styles that can make or break your team’s success.

Leadership has always been as much about people as it is about performance. Ken Blanchard, in his influential book, “The One Minute Manager”, put it simply: different strokes for different folks. (more…)
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Your first 100 days as CEO could define your entire legacy, here’s how to make every move count

When Tim Cook took over from Steve Jobs at Apple, the world watched with bated breath. Jobs wasn’t just a CEO; he was a visionary, an icon, and a legend of innovative leadership. (more…)
Entrepreneurs
The Leadership Shift Every Company Needs in 2025
Struggling to keep your team engaged? Here’s how leaders can turn frustrated employees into loyal advocates.

In workplaces around the world, there’s a growing gap between employers and employees and between superiors and their teams. It’s a common refrain: “People don’t leave companies, they leave bad bosses.”
While there are, of course, cases where management could do better, this isn’t just a “bad boss” problem. The relationship between leaders and employees is complex. Instead of assigning blame, we should explore practical solutions to build stronger, healthier workplaces where everyone thrives.
Why This Gap Exists
Every workplace needs someone to guide, supervise, and provide feedback. That’s essential for productivity and performance. But because there are usually far more employees than managers, dissatisfaction, fair or not, spreads quickly.
What if, instead of focusing on blame, we focused on building trust, empathy, and communication? This is where modern leadership and human-centered management can make a difference.
Tools and Techniques to Bridge the Gap
Here are proven strategies leaders and employees can use to foster stronger relationships and create a workplace where people actually want to stay.
1. Practice Mutual Empathy
Both managers and employees need to recognize they are ultimately on the same team. Leaders have to balance people and performance, and often face intense pressure to hit targets. Employees who understand this reality are more likely to cooperate and problem-solve collaboratively.
2. Maintain Professional Boundaries
Superiors should separate personal issues from professional decision-making. Consistency, fairness, and integrity build trust, and trust is the foundation of a motivated team.
3. Follow the Golden Rule
Treat people how you would like to be treated. This simple principle encourages compassion and respect, two qualities every effective leader must demonstrate.
4. Avoid Micromanagement
Micromanaging stifles creativity and damages morale. Great leaders see themselves as partners, not just bosses, and treat their teams as collaborators working toward a shared goal.
5. Empower Employees to Grow
Empowerment means giving employees responsibility that matches their capacity, and then trusting them to deliver. Encourage them to take calculated risks, learn from mistakes, and problem-solve independently. If something goes wrong, turn it into a learning opportunity, not a reprimand.
6. Communicate in All Directions
Communication shouldn’t just be top-down. Invite feedback, create open channels for suggestions, and genuinely listen to what your people have to say. Healthy upward communication closes gaps before they become conflicts.
7. Overcome Insecurities
Many leaders secretly fear being outshone by younger, more tech-savvy employees. Instead of resisting, embrace the chance to learn from them. Humility earns respect and helps the team innovate faster.
8. Invest in Coaching and Mentorship
True leaders grow other leaders. Provide mentorship, career guidance, and stretch opportunities so employees can develop new skills. Leadership is learned through experience, but guided experience is even more powerful.
9. Eliminate Favoritism
Avoid cliques and office politics. Decisions should be based on facts and fairness, not gossip. Objective, transparent decision-making builds credibility.
10. Recognize Efforts Promptly
Recognition often matters more than rewards. Publicly appreciate employees’ contributions and do so consistently and fairly. A timely “thank you” can be more motivating than a quarterly bonus.
11. Conduct Thoughtful Exit Interviews
When employees leave, treat it as an opportunity to learn. Keep interviews confidential and use the insights to improve management practices and culture.
12. Provide Leadership Development
Train managers to lead, not just supervise. Leadership development programs help shift mindsets from “command and control” to “coach and empower.” This transformation has a direct impact on morale and retention.
13. Adopt Soft Leadership Principles
Today’s workforce, largely millennials and Gen Z, value collaboration over hierarchy. Soft leadership focuses on partnership, mutual respect, and shared purpose, rather than rigid top-down control.
The Bigger Picture: HR’s Role
Mercer’s global research highlights five key priorities for organizations:
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Build diverse talent pipelines
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Embrace flexible work models
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Design compelling career paths
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Simplify HR processes
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Redefine the value HR brings
The challenge? Employers and employees often view these priorities differently. Bridging that perception gap is just as important as bridging the relational gap between leaders and staff.
Treat Employees Like Associates, Not Just Staff
When you treat employees like partners, they bring their best selves to work. HR leaders must develop strategies to keep talent engaged, empowered, and prepared for the future.
Organizational success starts with people, always. Build the relationship with your team first, and the results will follow.
Entrepreneurs
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